Yeah, this is how I was actually wearing them today, with looser jeans over the top of them. I usually wear slimmer pants with boots that have a slimmer top block, so I'm not sure of what to do with something slouchy like this. I'm just worried that loose pants + boots ventures too far into "dudes with ill-fitting bootcut pants and terrible boots" zone

SF's idea of loose and slim are fairly different from said "dudes." Your looser jeans fall under slim to skinny by a lot of people's standards.

^ Really? I think it can look amazing. Maybe it's different with japanese girls, they wear kinda shit here, a lot of cool layering so overalls (at least the few times I've seen it) don't look really out of place or very contrived as I imagine they can in other places. Also, in general, I like girls in baggy (in a good way) clothing.